As a direct consequence of the interplay between the superposition principle of quantum mechanics and the dynamics of open systems, decoherence is a recurring theme in both foundational and experimental exploration of the quantum realm. Decoherence is intimately related to information leakage of open systems and is usually formulated in the setup of “system + environment” as information acquisition of the environment (observer) from the system. As such, it has been mainly characterized via correlations (e.g., quantum mutual information, discord, and entanglement). Decoherence combined with redundant proliferation of the system information to multiple fragments of environment yields the scenario of quantum Darwinism, which is now a widely recognized framework for addressing the quantum-to-classical transition: the emergence of the apparent classical reality from the enigmatic quantum substrate. Despite the half-century development of the notion of decoherence, there are still many aspects awaiting investigations. In this work, we introduce two quantifiers of classicality via the Jordan product and uncertainty, respectively, and then employ them to quantify decoherence from an information-theoretic perspective. As a comparison, we also study the influence of the system on the environment.